63082-55-3Relevant academic research and scientific papers
Pd(0)-catalyzed allylic alkylation/Heck coupling in domino sequence
Poli, Giovanni,Giambastiani, Giuliano,Pacini, Barbara
, p. 5179 - 5182 (2001)
A new molecular queuing process has been achieved, in which a single Pd-based catalytic system promotes two unrelated, sequential catalytic cycles in chronologically distinct order. This study demonstrates also that allylic alkylations can be catalyzed by the Herrmann's phosphapalladacycle, a result that further supports the involvement of a Pd(0) species in its mechanism of action.
Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling
Davies, Stephen G.,Smith, Andrew D.,Cowley, Andrew R.
, p. 1957 - 1960 (2004)
The asymmetric three-component coupling of α,β-unsaturated esters and alkylidene malonates initiated with a homochiral lithium amide proceeds with high levels of diastereoselectivity, with hydrogenation of the resultant α-substituted β-amino acid derivatives giving a range of differentially protected 3,4,5,6-tetrasubstituted piperidinones with four contiguous stereogenic centres.
Derivatives of phosphorous acid as a new class of ligands for Pd-catalyzed allylation
Moiseev,Lebedev,Polosukhin,Kalinin
, p. 554 - 556 (2001)
Amido- and aminophosphites and hydrospirophosphoranes can be used as ligands in the Pd-catalyzed allylation of ethyl malonate with ethyl (3-phenylprop-2-enyl) carbonate. Bidentate ligands (RO)2P - O(CH2)n - NR′2
Copper-catalyzed regiodivergent 1,4-and 1,6-conjugate silyl addition to diendioates: Access to functionalized allylsilanes
Ahmad, Tanveer,Li, Qi,Qiu, Sheng-Qi,Xu, Jian-Lin,Xu, Yun-He,Loh, Teck-Peng
, p. 6122 - 6126 (2019/07/03)
A copper-catalyzed regioselective 1,4-and 1,6-conjugate addition of a silyl reagent to diendioates was established. Various 1,4-and 1,6-protosilylation products were obtained in good yields and with high regioselectivity via tuning the ligands used in the reactions. This protocol has provided a simple and efficient method for the synthesis of multisubstituted functionalized allylsilanes.
Highly selective palladium-benzothiazole carbene-catalyzed allylation of active methylene compounds under neutral conditions
Monopoli, Antonio,Cotugno, Pietro,Zambonin, Carlo G.,Ciminale, Francesco,Nacci, Angelo
supporting information, p. 994 - 999 (2015/08/19)
The Pd-benzothiazol-2-ylidene complex I was found to be a chemoselective catalyst for the Tsuji-Trost allylation of active methylene compounds carried out under neutral conditions and using carbonates as allylating agents. The proposed protocol consists in a simplified procedure adopting an in situ prepared catalyst from Pd2dba3 and 3-methylbenzothiazolium salt V as precursors. A comparison of the performance of benzothiazole carbene with phosphanes and an analogous imidazolium carbene ligand is also proposed.
Metal-free, regio- and stereoselective synthesis of linear (E)-allylic compounds using C, N, O, and S nucleophiles
Huang, Xiaojun,Fulton, Brandon,White, Kana,Bugarin, Alejandro
, p. 2594 - 2597 (2015/06/16)
A variety of allylic acetates and derivatives were synthesized by an efficient two-step protocol that employs readily available terminal alkenes as starting materials. This method is highly regio- and stereoselective, affording the linear (E)- isomer as the sole adduct. This process tolerates several functional groups including halogen-containing molecules, and it is general for weak oxygen, carbon, nitrogen, and sulfur nucleophiles. Furthermore, adducts were obtained in good to excellent yields.
Metathesis transformations of unsaturated derivatives of β-diketones
Mi?tkiewski, Mi?osz,Powa?a, Beata,Staniszewski, Bartosz,Kubicki, MacIej,Urbaniak, W?odzimierz,Pietraszuk, Cezary
scheme or table, p. 728 - 736 (2012/04/17)
Selected β-diketones bearing unsaturated derivatives have been demonstrated to undergo homo-metathesis and cross-metathesis with selected olefins in the presence of Grubbs catalysts. The reactions led to respective homo- and cross-metathesis products mainly with good yields and selectivities. Versita Sp. z o.o.
A novel hemilabile calix[4],quinoline-based P,N-ligand: Coordination chemistry and complex characterisation
Marson, Angelica,Ernsting, Johanneke E.,Lutz, Martin,Spek, Anthony L.,Van Leeuwen, Piet W. N. M.,Kamer, Paul C. J.
experimental part, p. 621 - 633 (2009/05/06)
The synthesis of the calix[4]arene-based P,N-ligand 3 (5,11,17,23-tetra- tert-butyl-25-[(2-quinolylmethyl)oxy]-26,27,28-(μ3- phosphorustrioxy)calix[4]arene), in which the nitrogen atom-containing moiety has been introduced at the lower rim of t
Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones
Davies, Stephen G.,Roberts, Paul M.,Smith, Andrew D.
, p. 1405 - 1415 (2008/02/10)
The efficiency and stereoselectivity of the conjugate addition of lithium (Z)- or (E)-β-amino ester enolates, generated by lithium amide conjugate addition to an α,β-unsaturated ester or deprotonation of a β-amino ester, respectively, to a range of α,β-unsaturated acceptors has been investigated. Deprotonation of a β-amino ester with LDA, followed by conjugate addition to a chiral α,β-unsaturated oxazolidinone gives high 2,3-anti selectivity (～90% d.e.), with hydrogenolysis and purification to homogeneity generating stereodefined trisubstituted piperidinones as single stereoisomers. Asymmetric three-component couplings of α,β-unsaturated esters and alkylidene malonates initiated by lithium amide conjugate addition proceeds with high levels of 2,3-anti stereoselectivity, with hydrogenolysis giving tetrasubstituted piperidinones. This journal is The Royal Society of Chemistry.
Catalytic deallylation of allyl- and diallylmalonates
Necas, David,Tursky, Matyas,Kotora, Martin
, p. 10222 - 10223 (2007/10/03)
Substituted allylmalonates undergo the selective C-C bond cleavage in the presence of triethylaluminum and a catalytic amount of nickel and ruthenium phosphine complexes, resulting in the loss of the allyl moiety and formation of monosubstituted malonates. Comparison of reactivity of the nickel and ruthenium complexes showed that the use of the former is general with respect to the structure of the substituted allylmalonates, and the activity of the latter depended on the substitution pattern of the double bond of the allylic moiety. The smooth deallylation may encourage the use of the allyl group as a protective group for the acidic hydrogen in malonates. Copyright
